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Volume 69 
Part 9 
Pages o1422-o1423  
September 2013  

Received 1 August 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.118
Data-to-parameter ratio = 17.1
Details
Open access

1-{2-[(E)-2-(2-Nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethanone

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C24H18N2O5S, the S atom has a distorted tetrahedral configuration, with bond angles varying from 105.11 (7) to 119.98 (8)°. As a result of the electron-withdrawing character of the phenylsulfonyl group, the N-Csp2 bond lengths [1.414 (2) and 1.413 (2) Å] are slightly longer than the reported value of 1.355 (14) Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177 (14) Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70 (7)° with the mean plane of the indole moiety. The molecular structure features intramolecular C-H...O hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent molecules are linked via C-H...O hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C-H...[pi] interactions, which form a three-dimensional structure.

Related literature

For the biological activity of Indole derivatives, see: Rodriguez et al. (1985[Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.]); Chai et al. (2006[Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Olgen & Coban (2003[Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.]). For related crystal structures, see: Karthikeyan et al. (2011[Karthikeyan, S., Sethusankar, K., Rajeswaran, G. G. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o2245-o2246.], 2012[Karthikeyan, S., Sethusankar, K., Rajeswaran, G. G. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o9.]). For related bond distances and bond-angle geometries and distortions, see: Allen (1981[Allen, F. H. (1981). Acta Cryst. B37, 900-906.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the Thorpe-Ingold effect, see: Bassindale (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18N2O5S

  • Mr = 446.46

  • Monoclinic, P 21 /n

  • a = 8.2409 (8) Å

  • b = 16.1702 (15) Å

  • c = 15.3700 (15) Å

  • [beta] = 95.775 (5)°

  • V = 2037.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 296 K

  • 0.28 × 0.25 × 0.23 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • 18837 measured reflections

  • 4960 independent reflections

  • 3893 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.118

  • S = 1.02

  • 4960 reflections

  • 290 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C17-C22, C11-C16 and C1-C6 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...O1 0.93 2.35 2.935 (2) 121
C18-H18...O3 0.93 2.46 3.108 (2) 127
C20-H20...O2i 0.93 2.68 3.319 (2) 126
C5-H5...Cg1ii 0.93 2.89 3.720 (2) 149
C22-H22...Cg2iii 0.93 2.73 3.4618 (18) 137
C24-H24B...Cg3iv 0.96 2.90 3.601 (3) 131
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+1; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2631 ).


Acknowledgements

The authors thank Mr T. Srinivasan and Dr D. Velmurugan, The Head, CAS in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.

References

Allen, F. H. (1981). Acta Cryst. B37, 900-906.  [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Karthikeyan, S., Sethusankar, K., Rajeswaran, G. G. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o2245-o2246.  [CSD] [CrossRef] [ChemPort] [details]
Karthikeyan, S., Sethusankar, K., Rajeswaran, G. G. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o9.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Olgen, S. & Coban, T. (2003). Biol. Pharm. Bull. 26, 736-738.  [CrossRef] [PubMed]
Rodriguez, J. G., Temprano, F., Esteban-Calderon, C., Martinez-Ripoll, M. & Garcia-Blanco, S. (1985). Tetrahedron, 41, 3813-3823.  [CSD] [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1422-o1423   [ doi:10.1107/S1600536813022241 ]

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